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78 Important Questions
Every Leader Should
Ask and Answer
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78 Important Questions
Every Leader Should
Ask and Answer
CHRIS CLARKE-EPSTEIN




A M E R I C A N M A N A G E M E N T A S S O C I AT I O N
N e w Yo r k Atlanta Brussels Buenos Aires Chicago
L o n d o n M e x i c o C i t y S a n F r a n c i s c o S h a n g h a i To k y o
To r o n t o W a s h i n g t o n, D. C.
Special discounts on bulk quantities of AMACOM books are available to corporations,
professional associations, and other organizations. For details, contact Special Sales
Department, AMACOM, a division of American Management Association, 1601
Broadway, New York, NY 10019.
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Web site: www.amacombooks.org


This publication is designed to provide accurate and authoritative information in regard to
the subject matter covered. It is sold with the understanding that the publisher is not
engaged in rendering legal, accounting, or other professional service. If legal advice or other
expert assistance is required, the services of a competent professional person should be
sought.




Library of Congress Cataloging-in-Publication Data

Clarke-Epstein, Chris.
78 important questions every leader should ask and answer / Chris
p. cm.
Includes bibliographical references (p. ) and index.
ISBN 0-8144-7162-5
1. Leadership. 2. Communication in organizations. 3. Corporate culture.
4. Public relations. I. Title: Seventy eight important questions every leader
should ask and answer. II. Title.

HD57.7. C539 2002
658.4'092--dc21
2002008308



© 2002 Chris Clarke-Epstein.
All rights reserved.
Printed in the United States of America.

This publication may not be reproduced, stored in a retrieval system, or transmitted in
whole or in part, in any form or by any means, electronic, mechanical, photocopying,
recording, or otherwise, without the prior written permission of AMACOM, a division of
American Management Association, 1601 Broadway, New York, NY 10019.

Printing number
10 9 8 7 6 5 4 3 2 1
To my mother, June Blomberg, who raised me in an envi-
ronment that encouraged me to ask questions¦lots of them.


To Stel Epstein and Miriam Phillips, who read everything I
write and have the courage to ask, “What were you thinking?”
This Page Intentionally Left Blank
contents


. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .XIII
PREFACE

How to Use This Book . . . . . . . . . . . . . . . . . . . . . . . . . . . XV
A Warning . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . XVII

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . XIX
ACKNOWLEDGMENTS


. . . . . . . . . . .1
INTRODUCTION: ANSWERS, YOU WANT ANSWERS

The Power and Problem of Why? . . . . . . . . . . . . . . . . . . . . 6


1 . . . . . . . . . . .9
QUESTIONS LEADERS NEED TO ASK THEMSELVES

1. What does leadership mean? . . . . . . . . . . . . . . . . . . . . . 11
2. How do you feel about being a leader?. . . . . . . . . . . . . . 13
3. What do you want to be remembered for? . . . . . . . . . . . 15
VIII CONTENTS




4. Are you happy?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17
5. What are you afraid of? . . . . . . . . . . . . . . . . . . . . . . . . 19

6. Are you sure you want to ask questions?. . . . . . . . . . . . 21
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
CHAPTER ONE WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . . 23


2 . . . . . . . . . . .27
QUESTIONS LEADERS NEED TO ASK CUSTOMERS

7. Why do you do business with us?. . . . . . . . . . . . . . . . . 30
8. Why do you do business with our competition?. . . . . . 31

9. How and when have we made it hard for you to
do business with us? . . . . . . . . . . . . . . . . . . . . . . . . . . . 33
10. What will you need from us in the future? . . . . . . . . . . 35
11. If you were me, what™s one thing you™d change about
my organization? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37
12. How can we effectively tell you that we™re grateful
for your business? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
. . . . . . . . . . . . . . . . . . . . . . . . 42
CHAPTER TWO WORKSHEET



3 QUESTIONS LEADERS NEED TO ASK EMPLOYEES
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .45
ABOUT THE BUSINESS

13. How do we make money?. . . . . . . . . . . . . . . . . . . . . . . 48
14. How does your work contribute to our success?. . . . . . 50

15. How could we save money? . . . . . . . . . . . . . . . . . . . . . 52

16. How could you make your job more effective?. . . . . . . 54
17. What™s the most important thing you know about our
customers? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55

18. What™s something we could offer to our customers?. . . 57
IX
CONTENTS




19. Who do you see as our competition, and what do you
know about them? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60
. . . . . . . . . . . . . . . . . . . . . . . 61
CHAPTER THREE WORKSHEET



4 DEEPER QUESTIONS LEADERS NEED TO ASK EMPLOYEES . . . . .63

20. What gets in the way of your doing your job? . . . . . . . 67
21. What does our leadership team do that gets in the
way of your doing your job? . . . . . . . . . . . . . . . . . . . . . 69
22. What™s a recent management decision you didn™t
understand? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71
23. How could we communicate management decisions
more effectively?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
24. If you could change one thing about our organization™s
collective behavior, what would it be?. . . . . . . . . . . . . . 75
25. What™s a potential benefit we could offer that would be
helpful to you? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
26. What is it like to work on a team in our organization?. 79
27. How do you feel at the start of your workweek?. . . . . . 81
28. How do you feel at the end of your workweek? . . . . . . 83
29. What volunteer work do you do? . . . . . . . . . . . . . . . . . 84
30. What makes you proud of working as a part of our
organization?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86
31. What™s something you™ve learned in the past week? . . . 88
32. What brings you joy in your work? . . . . . . . . . . . . . . . 90
33. What do you do just for the fun of it? . . . . . . . . . . . . . 92
34. What gives your life meaning? . . . . . . . . . . . . . . . . . . . 94
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95
. . . . . . . . . . . . . . . . . . . . . . . . 96
CHAPTER FOUR WORKSHEET
X CONTENTS




5 . . . . . . . . . . . . . .99
QUESTIONS TO ASK IN SPECIAL SITUATIONS

. . . . . . . . . . . . . . . . . . . 102
QUESTIONS FOR NEW EMPLOYEES

35. Why did you decide to join our firm¦really? . . . . 102
36. If you had to describe our organization in one word,
what would that word be? . . . . . . . . . . . . . . . . . . . 104
37. What™s a great question I could ask someone who™s
new to our organization? . . . . . . . . . . . . . . . . . . . . 106
38. What questions can I answer for you? . . . . . . . . . . 108

QUESTIONS FOR COACHING AND MENTORING SESSIONS . . . . 110
39. What are the strengths you bring to the workplace? . 110
40. What skills do you need to learn? . . . . . . . . . . . . . 112
41. What skills do you need to practice? . . . . . . . . . . . 113
42. Who in our organization do you need to know? . . 115
43. What work would you like to be doing in five years? 117

. . . . . . . . . . 118
QUESTIONS FOR NEWLY PROMOTED LEADERS

44. Why do you think we made you a leader? . . . . . . . 118
45. What did the best leader you ever had do?. . . . . . . 120
46. What do you need to learn to be a great leader? . . 121
47. How can we support you as you grow into this
leadership position? . . . . . . . . . . . . . . . . . . . . . . . . 123

QUESTIONS DURING A CRISIS . . . . . . . . . . . . . . . . . . . . . . . 125
48. Are you all right? . . . . . . . . . . . . . . . . . . . . . . . . . . 125
49. What do you need to know? . . . . . . . . . . . . . . . . . 127
50. What do you need? . . . . . . . . . . . . . . . . . . . . . . . . 129

. . . . . . . . . . . . . . . . . . . . . . . . . . . 130
WHAT DID YOU LEARN?

CHAPTER FIVE WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . 131
XI
CONTENTS




6 . . . . . . . . . . . . . . . .135
QUESTIONS LEADERS NEED TO ANSWER

51. What do you see happening in our organization over
the next twelve months? . . . . . . . . . . . . . . . . . . . . . . . 138
52. What is the future of our industry? . . . . . . . . . . . . . . 140
53. What gets you excited about the future?. . . . . . . . . . . 142
54. How do you learn about our customers? . . . . . . . . . . 144
55. How do you know what I do in my job? . . . . . . . . . . . 146
56. How can I advance in our organization?. . . . . . . . . . . 148
57. How do you make decisions? . . . . . . . . . . . . . . . . . . . 150
58. How do you take time to think? . . . . . . . . . . . . . . . . . 152
59. What makes you angry in the workplace?. . . . . . . . . . 155
60. How do you measure success? . . . . . . . . . . . . . . . . . . 157
61. What are you learning? . . . . . . . . . . . . . . . . . . . . . . . 159
62. How do you stay positive? . . . . . . . . . . . . . . . . . . . . . 161
63. How do you re-ignite your enthusiasm for your job? 163
64. What do you love about your job? . . . . . . . . . . . . . . . 165
65. What do you do just for fun? . . . . . . . . . . . . . . . . . . . 167
66. What gives your life meaning? . . . . . . . . . . . . . . . . . . 169
. . . . . . . . . . . . . . . . . . . . . . . . . . . 171
WHAT DID YOU LEARN?

CHAPTER SIX WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . . 172


7 . . . . . . . . . . . . . . . . . . .175
ANSWERS FOR SPECIAL SITUATIONS

DURING A BUSINESS CRISIS . . . . . . . . . . . . . . . . . . . . . . . . . 177
67. What™s happening? . . . . . . . . . . . . . . . . . . . . . . . . . 177
68. What™s going to happen next? . . . . . . . . . . . . . . . . 178
69. What™s going to happen to me? . . . . . . . . . . . . . . . 179
70. Am I going to have a job next month? . . . . . . . . . . 180
XII CONTENTS




71. What™s the long-term impact of this crisis? . . . . . . 181
. . . . . . . . . . . . . . . . . 182
DURING A MERGER OR ACQUISITION

72“73. What™s going to change? What™s going to happen
to my job? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 182
74. Who will be my leader? . . . . . . . . . . . . . . . . . . . . . 184
75. Will our values last? . . . . . . . . . . . . . . . . . . . . . . . . 185
DURING THE PERSONAL CRISIS OF AN EMPLOYEE . . . . . . . . 186
76“78. What will the organization do to support me?
What are my benefits? What will this mean
for my career? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 186
. . . . . . . . . . . . . . . . . . . . . . . . . . . 188
WHAT DID YOU LEARN?

. . . . . . . . . . . . . . . . . . . . . . 189
CHAPTER SEVEN WORKSHEET



8 . . . . . . . . . . . . . . . . . . . . . . .191
DELIVERING TOUGH ANSWERS

Answering when the answer is I don™t know . . . . . . . . . . . . 193
Answering when the answer is No. . . . . . . . . . . . . . . . . . . 194
Answering when there isn™t an answer . . . . . . . . . . . . . . . 195
Answering when you can™t answer . . . . . . . . . . . . . . . . . . 196
Answering when no one wants to hear the answer . . . . . . 197
Answering a question that™s just too personal . . . . . . . . . . 198
. . . . . . . . . . . . . . . . . . . . . . . . . . . 199
WHAT DID YOU LEARN?

. . . . . . . . . . . . . . . . . . . . . . 200
CHAPTER EIGHT WORKSHEET


. . . . . . . . . . . . . . . .203
CONCLUSION: SOME FINAL QUESTIONS


. . . . . .207
APPENDIX: GOOD QUESTIONS FROM OTHER LEADERS


. . . . . . . . . . . . . . . . . . . . . . . . . .212
SUGGESTED READING LIST


. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .215
INDEX
preface


Captain Jean-Luc Picard looked up from his log,
checked the chronometer and decided that he had
spent enough time in his ready room for one day. Time
to get up and walk about a bit, get the feel of the ship
under his feet. A crew had moods and the only way to
find out what they are is to go out and tread the deck.
Of course, he could just call in either Riker or Troi and
put the question to them”How is the crew feeling?”and
from their different perspectives form a clear and reli-
able picture. Over the years, Picard had learned that
this method omitted an essential component. If he
stayed in his ready room and waited for subordinates
to bring him answers, the crew wouldn™t know how
XIV P R E FA C E




Picard was feeling, at least, how Picard wanted them to
think he was feeling.
”Jeffrey Lang, Immortal Coil


When Tom Peters wrote In Search of Excellence in 1982, he intro-
duced leaders all over the world to the concept of Managing by
Wandering Around (MBWA). As a consultant and facilitator for
management teams, I™ve discovered how difficult it is for many lead-
ers to get up from behind their desks, or more frequently, to excuse
themselves from yet another meeting and place themselves in close
proximity to the people they are leading. One day it dawned on me
that getting them in front of their people isn™t even the hardest part.
All too often, they don™t know what to say once they get there!
You might have assumed that from the moment you were given
the title of leader, you were required to be the source of all wisdom.
In other words, you were supposed to be the person answering

It is not the answer that en-
lightens, but the question.
”Eugene Ionesco,
Romanian playwright



questions, not asking them. Nothing could be further from the
truth. Good leaders are humbled by the realization of all they do
not know, and they quickly reach the conclusion that they™d better
find some trusted advisers and ask a few questions. Great leaders
know that asking questions of a few won™t give them enough data.

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